Sodium Carbonate → N-(5,6-Dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-O-ethyl-hydroxylamine

HRID 2358473ノート

反応式

HRID 2358473 の反応式
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=O)[CH2:8]2.Cl.[CH2:17]([O:19][NH2:20])[CH3:18].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([NH:20][O:19][CH2:17][CH3:18])[CH2:8]2

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 76850O-ethylhydroxylamine hydrochlorideHCID 46107525,6-dimethoxy-3,4-dihydro-1H-naphthalen-2-one

生成物 1

HCID 11218938N-(5,6-Dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-O-ethyl-hydroxylamine収率 45.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
10 °C

実験手順

5,6-Dimethoxy-3,4-dihydro-1H-naphthalen-2-one (1.5 g, 7.5 mmol), prepared as described in J Med. Chem. 1977, 20, 1111-1116, was dissolved in water (15 ml) and a solution of O-ethylhydroxylamine hydrochloride (1 g, 10 mmol) and Na2CO3 (0.53 g, 5 mmol) in water (10 ml) was added dropwise under stirring at 10° C. The reaction was left at room temperature overnight and then extracted with diethyl ether. The ether solution was evaporated to dryness under vacuum. The residue was dissolved in 20 ml of ethanol and concentrated hydrochloric acid (1 ml) and hydrogenated at 3,6×106 Pa (50 psi) using PtO2 as catalyst. The solvent was removed under reduced pressure, water was added and the aqueous phase was treated with NaHCO3 and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated to dryness under vacuum. The crude residue was purified by chromatography, to afford 0.85 g of the title compound.

後処理

  1. extractionextracted with diethyl ether
  2. customThe ether solution was evaporated to dryness under vacuum
  3. dissolutionThe residue was dissolved in 20 ml of ethanol
  4. customThe solvent was removed under reduced pressure, water
  5. additionwas added
  6. additionthe aqueous phase was treated with NaHCO3
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under vacuum
  11. customThe crude residue was purified by chromatography

出典と根拠

ORDレコード
ord-83347ca327944445b6616c14582a3364
出典データセット
uspto-grants-2010_07
特許番号
US07763751B2

反応ノート

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